City Cast Portland logo
Advertisement image

Get To Know Portland's Woodlawn Neighborhood and Beyond

Posted on June 26, 2024   |   Updated on September 30, 2025
City Cast Portland staff

City Cast Portland staff

Blue splash pad with kids running through it

The splash pad at Woodlawn Park. (Portland Parks and Recreation)

Executive producer John Notarianni contributed the interview for this segment.

Leah Benson’s now-shuttered shop Gladys Bikes was a beloved spot in Portland when it was open. So we asked Benson, who recently also offered some of her best bike-buying advice, to share her favorite places in Portland — the locations that make this city her home:

“I am lucky enough to live right by the park, which is one of the most incredible parks in Portland. It's the perfect place for movies in the park. It's also a really great space for birding, if you're into that type of thing.”

“Woodlawn Coffee and Pastry is like my main girlfriend. I've been going for over 10 years now. I love just ordering a mug of coffee and hanging out there and seeing everyone from the neighborhood come.

“They have great pastries. Specifically, they have this blueberry cornmeal muffin that I don't think the recipe has changed in the entire time I've gone there and I love that.

“The other thing I like about it is the staff. I am officially no longer young and cool, and the staff there definitely is and they are currently playing my version of oldies these days. I went in the other day, and they had on John Mayer. They were talking about him like he was cool and they were like ‘My mom was really into him before.’ I'm like, ‘Oh shit I'm that person now,’ and I love it.”

“I had a friend that was… showing Superman cartoons and doing live instrumentation and voice acting for them… I fell in love with the Superman orchestra. I'm like, ‘How is this even a thing?’ It's so cool. And while that's not something that the Hollywood does anymore, you just can see things there that you can't find anywhere else in this city or this country.

“I love going to Kung Fu Theater on Tuesdays. I love queer horror, all of the weird little things that they do, and also that seemingly this entire city loves them.

“When you go in there, the staff acts like you're their best friend, which I just love. There is nothing better than being a regular in this world.”

‘Anything That Is on Top of a Hill’

“I always want to go to and ride my bike to Rocky Butte, Pittock Mansion, Tabor, Council Crest. I love the hills here. I don't care about views of mountains, but I really like riding up the hill.”

What places make Portland feel like home to you? Please email me.

City Cast

How To Buy Your Perfect Portland Bicycle

00:00:00
Your Favorite Homey Spots?

Share article

Hey Portland

Stay connected to City Cast Portland and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.

Neighborhood Guides

See All
Neighborhood GuidesFebruary 3

Your Guide to Oregon City

To Portland, Oregon City may be just a small suburb. (If you don’t even really know where it is, take 99 south past the Goodwill Bins and...

Pink, purple and yellow sunset views of the Willamette River at Willamette Falls
Neighborhood GuidesJanuary 21

Get To Know South Burlingame

Portland's South Burlingame neighborhood is small, but mighty. From lively cemeteries to neighborhood gems, here's everything you need to...

View of autumn trees at a cemetery.
Neighborhood GuidesDecember 8, 2025

Your Guide to an East Portland Neighborhood You’ve Probably Never Heard Of

Maybe you’ve never heard of the East Portland neighborhood Russell. But now you have: It’s an affordable, safe, and largely residential n...

trees line a paved path
Neighborhood GuidesNovember 10, 2025

The Neighborhood Hotspots in Family-Friendly West- and Eastmoreland

The charm of the Eastmoreland and Westmoreland neighborhoods is how great they are for the families that live there. Willamette Week’s ar...

people at tables at Monty's Red Sauce, Portland, Oregon
Neighborhood GuidesOctober 20, 2025

Your Guide to Hood River's Fruit Loop

Out near Hood River there’s a cluster of orchards and wineries along a 35-mile stretch of country roads. The area now goes by the attenti...

flowers in the foreground, Mount Hood in the background
Neighborhood GuidesSeptember 10, 2025

The Portland Neighborhood for Living in the Woods

Arnold Creek is a Portland neighborhood that you may never have heard of — maybe because it’s just barely inside city limits in Southwest...

map of Arnold Creek neighborhood. With Tryon Creek at the eastern edge.
Neighborhood GuidesAugust 14, 2025

Sunnyside Has Nickel Arcade Games and Peacock Lane

Sunnyside is a classic inner eastside neighborhood, with tree-lined streets. It’s walkable and bikeable. There’s Southeast Hawthorne for...

a Victorian house at night with red light in the top windows, Foxtrot, Portland, Oregon
Neighborhood GuidesJuly 21, 2025

Finding Old Portland in Foster-Powell's Back Alleys

Foster-Powell has the charms of Old Portland, with a maze of alleys where neighbors hang out. “I like the alleys; I think they're special...

pink tree in bloom on a back alley, Foster-Powell, Portland, Oregon

The latest in Portland

The Weekly Wander by City Cast PortlandJuly 12

Side Quest: Drinks with a View? Wine Not

Competition in Willamette Valley is fierce, but Amaterra sets the bar high (on top of the West Hills, in fact). It's 15 minutes from down...

People sit in red adirondack chairs at Amaterra Winery, looking out over the Tualatin Valley and a sloped vineyard. The setting sun peeks through a stand of tall evergreen trees.
The Weekly Wander by City Cast PortlandJuly 12

Your Guide to Portland's West Hills

The West Hills are a peaceful place to live with plenty of dining appeal, as restaurants and breweries keep heading to the ‘burbs.

Blueberries, some ripe and some not, weigh a branch down.
The Weekly Wander by City Cast PortlandJuly 5

Your Guide to Hosford-Abernethy

The history of this Portland, Oregon, neighborhood is rooted in the railroad industry, so Hosford-Abernethy is a fitting home for the Ore...

Crowds of people explore the exterior of the Oregon Rail Heritage Center, which has criss-crossing tracks and several locomotives, one of which sits on a working turntable.
The Weekly Wander by City Cast PortlandJuly 5

Side Quest: Tapas? Heck Yes

Meet vya, the Portland, Oregon, Spanish tapas restaurant that opened earlier this year in the former Palomar space, setting the scene for...

A hand squeezes a roasted lemon on top of a pan of paella with shrimp and mussels.
Portland's BestJuly 1

What To Do in Portland in July 2026

A quarter millennium ago, the U.S. got its start. Since then, we've experienced all the promises and disappointments of our country's rhe...

Parade with people in pink and rainbows.
Portland Life HacksJuly 1

Tips for a Better July 2026 in Portland

Find ways to prepare yourself for July in Portland, including tips on farmers markets, swimming, and fire season.

Pink, purple, and red flowers in a bouquet with pink tissue paper.
The Weekly Wander by City Cast PortlandJune 28

Your Guide to Maywood Park

Nestled where I-205 and I-84 meet, you’ll find a piece cut out of the Portland map. That’s Maywood Park, the enclave with a decidedly sma...

People pose in the street holding flags and a sign that says “City of Maywood Park” for the Fourth of July parade.
The Weekly Wander by City Cast PortlandJune 28

Side Quest: Trash to Treasure

Another big event on the Maywood Park calendar is the annual garage sale, where residents bring their unwanted items to Maywood Commons.

A colorful array of clothes on hangers at a bustling outdoor market.